Sodium Azide → 4-(2-((3-(Azidomethyl)oxetan-3-yl)methoxy)-3,4-dimethoxyphenyl)-indan-1-one

HRID 2171035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171035
CS(O[CH2:6][C:7]1([CH2:11][O:12][C:13]2[C:18]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH2:22][C:23]4=[O:28])=[CH:17][CH:16]=[C:15]([O:29][CH3:30])[C:14]=2[O:31][CH3:32])[CH2:10][O:9][CH2:8]1)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C)C=O>[N:33]([CH2:6][C:7]1([CH2:11][O:12][C:13]2[C:14]([O:31][CH3:32])=[C:15]([O:29][CH3:30])[CH:16]=[CH:17][C:18]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:10][O:9][CH2:8]1)=[N+:34]=[N-:35]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 86677576(3-((2,3-dimethoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)oxetan-3-yl)methyl methanesulfonate

Produkt 1

HCID 866775774-(2-((3-(Azidomethyl)oxetan-3-yl)methoxy)-3,4-dimethoxyphenyl)-indan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring solution of (3-((2,3-dimethoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)oxetan-3-yl)methyl methanesulfonate (5 g, 10.82 mmol) in dimethylformamide (40 mL), was added sodium azide (3.5 g, 54.11 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 4-(2-((3-(azidomethyl)oxetan-3-yl)methoxy)-3,4-dimethoxyphenyl)-indan-1-one as a solid.

Aufarbeitung

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with ice water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d18b2d3526954c5a96d5e87f5dc640d8
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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